ORGANIC
CHEMISTRY I (CHEM 2114) SYLLABUS
Instructor: ________________________________
Phone: 682-1611 Ext.
____________________
EMAIL: ________________________________
Office
Location: ________________________________
Office
Hours: ________________________________
LEARNING MATERIALS:
Textbook:
Wade, Jr., L. G. Organic
Chemistry, Seventh Edition, Pearson Prentice Hall, Inc., 2009.
OR
Wade,
Jr., L.G., Organic Chemistry, Sixth Edition,
Pearson Prentice Hall, Inc., 2006.
Other Materials: Darling
Molecular Model Set (recommended)
Simek, Jan William, Solutions
Manual Organic Chemistry, Seventh (or Sixth) Edition (by L.G. Wade, Jr),
Pearson Prentice Hall, Inc, 2006 (Optional)
COURSE DESCRIPTION:
Prerequisite: (R), (W), CHEM 1215. A grade of “C” or better in CHEM 1215 is REQUIRED.
4
CREDITS. This course is the first of a
two-semester sequence of Organic Chemistry for science and chemical engineering
majors as well as students seeking to enter the fields of medicine, dentistry,
pharmacy, and veterinary medicine.
Students will master the fundamental concepts of structure, functional
groups, and reactions of aliphatic compounds along with selected reaction
mechanisms.
COURSE COMPETENCIES:
Upon
completion of this course, students will be able to apply the principles and
theories of organic chemistry to interpret and explain fundamental chemical
phenomena, predict and explain the properties of organic compounds, predict the
products formed in organic reactions, apply organic reactions to the synthesis
of specified compounds, write an appropriate mechanism for selected organic
reactions, and interpret IR spectra. Through
a series of exams, students will demonstrate a mastery of the concepts of
bonding theory, stereochemistry, infrared spectroscopy, conformational
analysis, free radical reactions, nucleophilic substitution and elimination
reactions, oxidation and reduction of organic compounds, and reactions of
organometallic reagents. Students will
also demonstrate a basic knowledge of the chemistry of alkanes, alkyl halides,
alkenes, alkynes, alcohols, and ethers.
A list of specific learning objectives relating to these general
competencies is attached.
ACCOMMODATIONS FOR STUDENTS WITH
SPECIAL NEEDS
ASSESSMENT OF STUDENT LEARNING
To ensure that adequate assessment information is available to allow OCCC
to continuously improve programs and services, you may be asked to participate
in personal interviews; take program and/or general education assessments,
which could be tests; give oral presentations, write assignments, take surveys,
or engage in other activities. You may be asked to complete the
assessments, tests, and other activities during designated times, which may
include class periods. These opportunities are your chance to help OCCC
improve the courses, programs, and services which could affect you and will
certainly impact students in the future.
ATTENDANCE:
EMAIL:
Your OCCC email account (it has the form your.name@email.occc.edu) is
your official school email account. You
will be held responsible for any course information that comes to you via OCCC
email, so be sure to check it regularly throughout the semester.
WITHDRAWAL:
If you stop attending
and do not plan on finishing the course, you must withdraw yourself from the
course prior to the 12th week of class. The
instructor cannot administratively withdraw you. Withdrawal deadlines are published in the
College Class Schedule. When you withdraw from a course, the grade on your
permanent transcript is a "W" (Withdrawn). The grade of "W"
has no impact on your grade point average.
Grading:
The grade assigned
for this course will be determined by your performance on unit exams, a
comprehensive final exam, review assignments, and IR worksheets. Detailed information about each of these
grading areas is outlined below.
Six
unit exams will be given during the semester.
You are expected to take all exams in class. If you miss the in-class exam, you must take
the make-up exam in the
If
you take a unit exam in class and receive less than 60%, you may re-take that
exam. You will receive the higher score
from the two exams up to a maximum of
70%. All re-tests must be completed
within 14 days of the day the exam was given in class. You
are limited to a maximum of 2 make-up exams and/or re-tests (combined) on the
unit exams during the semester.
Make-up exams and re-tests are
generally not available for Unit 6. Any make-up or retest for the Unit 6 exam
must be approved by your instructor and must be taken by the final class period
or the deadline set by your instructor.
Comprehensive Final – 1 final exam
x 100 points = 100 points
The
comprehensive final exam will be given in class on the last day of the
semester. Up to 20% of the points on
this exam will come from concepts covered in General Chemistry I and II. Objectives for both the Organic I and General
Chemistry portions of this exam are given later in the syllabus. You are expected to take the comprehensive
final exam in class. You may not re-test on the comprehensive
final. A make-up exam will be given only under extraordinary circumstances
(as defined and approved by your instructor).
In order to receive an “A,” “B,”
or “C” in the course, a student must earn the minimum final exam score
described in the table in the “Grading Scale” section. Failure to achieve the minimum final exam
score will result in a one letter grade reduction in the student’s overall
course grade. See the “Grading Scale” section for details.
You will complete two review assignments during the
semester. You are expected to complete
these assignments independently,
receiving no help from anyone other than your instructor. The review assignment is due at the start of
class on the dates listed in your lecture schedule. Late
review assignments will be accepted through
the beginning of the class period following the due date and will be
subject to a 5 point penalty, even if you were absent on the day the
assignment was handed out to the class.
Two IR worksheets will be assigned during the semester. You are expected to complete each assignment independently,
receiving no help from anyone other than your instructor. Due dates for the assignments are indicated
on your class schedule. Late IR assignments will be accepted
through the beginning of the class period following the due date and
will be subject to a 5 point penalty.
Working the homework problems assigned in the
syllabus is an integral part of the learning process. Although homework will not be collected or
graded, you are responsible for all of the concepts and skills covered by these
problems. Be prepared! Some of these homework problems may appear on quizzes or exams.
Grading Scale:
Total points
possible = 600 + 100 + 40 + 40 = 780 points
Your
course grade will be determined primarily using the overall percentage of
points earned during the course.
However, in order to receive an
“A” or “B” in the course, you must score at least 70.0% on the comprehensive
final exam. In order to receive a “C” in
the course, you must score at least 60.0% on the comprehensive final exam. See the grading scale table below.
Failure to satisfy the minimum
final exam score requirements will result in a one letter grade reduction in
your overall course grade. For example, a student who earns 95.3% of the
780 points possible but scores a 69.5% on the comprehensive final exam will
receive a “B” in the course. Similarly,
a student who earns 79.2% of the 780 points possible but scores a 59.5% on the
comprehensive final exam will receive a “D” in the course.
|
Grade |
% |
Minimum
Final Exam Score |
|
A |
90.0 – 100 |
70.0% |
|
B |
80.0 – 89.9 |
70.0% |
|
C |
70.0 – 79.9 |
60.0% |
|
D |
60.0 – 69.9 |
none |
|
F |
59.9 or less |
none |
ACADEMIC DISHONESTY
Students are expected
to adhere to the standards of conduct outlined in the OCCC Student
Handbook. Academic dishonesty will not be tolerated. Academic dishonesty, including but not
limited to bringing and/or using unauthorized information to exams, disclosing
the contents of exams to other students, making written or electronic copies of
questions from exams, copying information from other students, or allowing
other students to copy your answers on review assignments, worksheets, or exams,
will result in a zero for the assignment or a failing grade for the
course. Other appropriate penalties, as
determined by your instructor, may also be imposed. A record of the incident will be forwarded to
the Offices of the Dean of the Division and the Vice-President for Academic
Affairs.
TRANSFERABILITY
It is the understanding of the Chemistry
Program that this course will transfer to the
SAFETY AND SECURITY
EMERGENCY PROCEDURES
The health
and safety of all our students, faculty, and staff are OCCC's prime
concern. The procedures outlined below
are designed to deal with emergencies of various types. Students should always follow the lead of
their instructors.
Fire
First
notification will come from the fire alarm horns, sirens, and strobes. The class should gather their belongings,
exit the building using the nearest exit, and move to a parking lot. Do not
use the elevators. No alarm should
be treated as a false alarm. Horns,
sirens, and strobes are only used for fire alarms.
Fire (Special Considerations)
If someone
in your area is not physically capable of descending the stairwell, please
ensure that they remain in the "area
of safe refuge" located just inside each upper-level enclosed fire
stairwell. There are emergency phones
located near each of these areas.
Medical
For all
medical related issues push the "emergency"
button located on each classroom phone.
The phone will display your room number, allowing for fast response to
your location. All security officers are
trained as first responders and will assist in guiding EMSA to your location. Treat all bodily fluids as if they were
contaminated.
Bomb
If you receive
a bomb threat, document as much information as possible and push the "emergency" button on the
phone. If the decision to evacuate is
given, the phone will sound an alarm
and display a text message. The class should gather their belongings,
exit the building using the nearest exit, and move to an open grassy area. Please turn off all wireless devices. (Cell
phones, radios, laptops, and other portable devices.)
Weather
Tornado
warnings that include OCCC will be sent directly to the classroom phone. The phone will sound an alarm and display
a text message. The class should gather
their belongings, move away from exterior glass and exits, and move to safer
areas. These areas are lower-level
interior classrooms, restrooms, and stairwells.
You should familiarize yourself with the safer areas near your
classroom(s). If the city/county sirens
are sounding and OCCC is not in the
warning area a message will be sent to the classroom phone advising this
information.
Disturbance/Threats
If someone
is causing a disturbance in a classroom, call security immediately. Push the "emergency" button located on each classroom phone. Distance yourself from that person, do not
place yourself in the person's exit path and remove all potential weapons from
the area. Shelter in place: If there
is an armed person or shooter on campus:
Close and lock your hallway doors.
Turn off the lights, shut the blinds or move away from exposed
areas. Use desks, tables and other
objects to provide protection. Updated
information will be sent to the classroom phone.
Organic
Chemistry I Objectives
Unit
1 Objectives
Chapter 12 (Sections
12-1 to 12-12)
Homework: 1-2, 1-3 (a,b,d,f), 1-5 (a-c), 1-6, 1-7 (d,e,g), 1-8,
1-9, 1-10, 1-11, 1-12 (a,b), 1-15, 1-17, 1-18, 1-19, 1-21, 1-23, 1-25,
1-26, 1-27, 1-28, 1-34, 1-35 (part 1 only), 1-36, 1-37, 1-40, 1-41, 1-44, 1-45, 1-46, 1-49, 2-5, 2-8, 2-14,
2-16, 2-17, 2-18, 2-20, 2-21, 2-22,
2-27, 2-28, 2-32 (d), 2-33, 2-36, 2-37,
2-39, 2-40, 2-41, 2-42, 2-44
IR Homework: 12-2, 12-3,
12-4, 12-5, 12-6, 12-15 (omit a and b), 12-16, 12-25, 12-28
NOTE:
Homework problems shown in bold type are ones that you MUST do. The others listed are highly recommended for
those students who want to do well on the unit quiz and exam.
1.
Define and/or
recognize definitions or descriptions of the terms listed in the glossaries at
the end of the reading assignment. Be
able to recognize or cite examples of each.
2.
Draw
structural formulas of organic compounds belonging to the families listed
below. Be able to classify compounds
according to their functional group and to identify all of the functional
groups present in a compound:
a. alkanes f. alcohols k. carboxylic acids
b. alkenes
g. ethers
l. acid chlorides
c. alkynes h. amines
m. amides
d. aromatic ring i. aldehyde n. esters
e. alkyl halides j. ketones
o. nitriles
3.
Given the
structure or formula for an amine or amide, classify it as primary, secondary,
or tertiary.
4.
Identify any
polar covalent bonds present in a given substance. Identify all partial charges that would exist
on a molecule of that substance and depict the direction of the bond dipole
moment.
5.
Draw Lewis structures
for molecules (or ions) and position formal charges on atoms.
6.
Draw resonance
structures for representative compounds, ions, or free radicals that follow all
rules for resonance structures. Identify
or draw major resonance structures of a given substance.
7.
Given a
compound represented as a Lewis structure, structural formula, condensed structural
formula, line-angle drawing, or three-dimensional structure, represent the
molecule using any of the other possible structures or formulas.
10.
Given a
chemical reaction, identify the Bronsted-Lowry acid and base as well as the
conjugate acid and conjugate base that are present. Given a chemical reaction, identify the Lewis
acid (electrophile) and Lewis base (nucleophile) present.
11.
Recognize
common acids used in organic synthesis including carboxylic acids, phenols,
alcohols, inorganic acids, and water. Recognize
common bases used in organic synthesis including amines, alcohols, water, and bases
that contain hydroxide, alkoxide, hydride, or amide ions.
12.
Given the
reactants in an acid/base reaction, give the structures and/or formulas of the
products of the reaction. Use curved
arrows to correctly show how the products are formed.
13.
Given a list
of compounds, rank the compounds in order of their relative acidity. Identify the stronger acid and stronger base
in a chemical equation and use that information to determine if the equilibrium
favors reactants or products.
14.
Use curved
arrows to show the movement of electrons in chemical reactions or the inter-conversion
of two resonance structures.
15.
Given a table
of the major IR stretching frequencies for organic molecules, interpret the IR
spectrum for an organic compound by assigning the major peaks to specific types
of bonds, determining the functional group(s) present in the molecule, and
drawing or recognizing a reasonable structure for the molecule. (NOTE: This material will be presented during Unit
1. You will be responsible for using
this material to complete the two IR assignments at the end of Unit 1 and the
beginning of Unit 2. Unit 1 exam will
not contain questions from this objective.
You will also be responsible for this objective on the Unit 2 exam.)
16.
You will be
able to answer questions or solve problems incorporating material from General
Chemistry with the current unit objectives.
In particular, the following objectives were covered in
either CHEM 1115 and/or CHEM 1215. These
objectives will not be
covered (or covered in detail) in this unit.
You are responsible for reviewing this material and must be prepared to
answer questions related to them on this and subsequent exams.
a.
Given a
periodic table, write electron configurations or draw orbital diagrams for any
of the following elements: C, H, N, O, S, P, the halogens, B, Al, Mg, Na, K,
and Li. Determine the number of valence
electrons for any main group element and draw a Lewis symbol for that element.
b.
Define and/or
distinguish ionic, covalent, and polar covalent bonds. Identify a compound as either ionic or
covalent. Compare ionic and covalent
compounds with respect to differences in boiling points, melting points,
physical states (at room temperature), and water solubilities.
c.
Predict the
shape of a molecule, using VSEPR theory.
From the shape of the molecule and the electronegativities of the bonded
atoms, predict if the molecule is polar or nonpolar and identify the direction
of the net molecular dipole moment for any polar molecules.
d.
Identify the
intermolecular force(s) that impact the physical properties of a given compound.
e.
Predict which
of two specified compounds is likely to have the higher boiling point based on
the hydrogen bonding, dipole-dipole forces, and London disperson forces acting
on the molecules.
f.
Predict the
type of bond hybridization, if any, occurring in compounds in which C, N, and O
are the central atoms and be able to predict the geometry of the bond.
g.
Given an
equation with the formulas of reactants and products, balance the
equation. Given the amount of a reactant
used or product formed, calculate the amount of any other reactant needed or
product formed in the reaction. Given
the mass of the reactants used in a reaction, calculate the theoretical yield
and percent yield of the reaction.
h.
Given
appropriate data, be able to calculate the empirical or molecular formula for a
compound.
UNIT 2: The Alkanes and Chemical
Reactions
Chapter 12 (Sections 12-1
to 12-12)
Homework Problems: 3-1, 3-3, 3-4, 3-5, 3-6, 3-7, 3-14, 3-16, 3-17, 3-21, 3-24, 3-27, 3-29, 3-30, 3-33, 3-34, 3-37, 3-38, 3-39, 3-40, 3-42, 3-44, 4-9a, 4-11, 4-12, 4-15,
4-16, 4-25a, 4-26, 4-29, 4-30, 4-32, 4-35, 4-38, 4-39, 4-41, 4-43, 4-44, 4-45a, 4-46, 4-50
IR Homework: 12-2, 12-3,
12-4, 12-5, 12-6, 12-15 (omit a and b), 12-16, 12-25, 12-28
NOTE:
Homework problems shown in bold
type are ones that you MUST do. The
others listed are highly recommended for those students who want to do well on
the unit quiz and exam.
1.
Define and/or
recognize definitions of the terms given in the glossaries at the end of the reading
assignment. Be able to recognize or cite
examples of each.
2.
State or
recognize the general formulas and structures for alkanes and cycloalkanes (CnH2n+2 and CnH2n) and apply
them to predicting or recognizing molecular formulas for those compounds.
3.
Recognize
and/or write formulas for constitutional isomers of specified compounds in
which the longest continuous chain contains five, six, seven, or eight carbons.
4.
Apply IUPAC
conventions for the nomenclature of alkanes and cycloalkanes to naming and drawing
formulas of specified compounds through decane, including straight-chain,
branched-chain, and cyclic compounds. Use in proper context (i.e., naming and
drawing formulas) alkyl group names including methyl, ethyl, propyl, isopropyl,
butyl, sec-butyl, isobutyl, tert-butyl, and neopentyl. Be able to designate
carbons as primary, secondary or tertiary.
5.
Describe
and/or recognize statements describing the general trends for the boiling
points, melting points, densities, and solubilities of alkanes corresponding to
(a) variations in chain length for a homologous series, (b) straight-chain
versus cyclic molecules, and (c) branched-chain versus straight-chain
molecules. Predict which member of a stated pair of compounds would have the
greater boiling point.
6.
Draw and/or
recognize the Newman projections representing the staggered, skew, and eclipsed
conformations of ethane, and the anti-, gauche, and eclipsed conformations of
butane. Assign each conformation to a
graph of potential energy versus rotation, or sketch such a graph. Know the basis for the energy barriers to
rotation.
7.
Given heat of
combustion data for various isomeric compounds, predict which would be most
stable.
8.
Delineate the
main factors involved in ring strain.
9.
Draw and/or
recognize drawings of the chair, boat, and twist-boat conformations of
cyclohexane. Identify axial and equatorial hydrogens on the chair conformation.
Predict which of the two possible chair conformations of a monosubstituted
cyclohexane is the more stable.
10.
Draw and/or recognize
drawings of the cis and trans isomers of disubstituted cycloalkanes and of the
alternate chair conformations of each isomer. Predict which of the alternate
chair conformations is the more stable.
11.
State the
reagents needed and the products formed by the combustion, cracking,
hydrocracking, and free radical halogenation reactions of alkanes.
12.
Draw the
complete mechanism for free radical halogenation of any alkane or cycloalkane.
13.
Use bond
dissociation energy values to predict the likelihood of homolytic reactions.
14.
Use the
relative stability of methyl, primary, secondary, tertiary, allyl, substituted
allylic, and vinyl free radicals and carbocations (carbonium ions) to rank a
series of free radicals or carbocations in order of stability.
15.
Explain the
relative reactivity of the halogens towards halogenation of methane and the
selectivity of bromine in free radical halogenation compared to chlorine.
16.
Predict the
major product formed by free radical halogenation of a hydrocarbon.
17.
Use the rate
equation to determine the impact that a change in concentration of one or more
reactants will have on the rate of a reaction.
18.
Be able to
draw and/or use an energy profile to discuss or determine transition states,
activation energies, intermediates, heat of reaction, and the rate determining
step of a reaction.
19. Given a table of the major IR stretching frequencies for
organic molecules, interpret the IR spectrum for an organic compound by
assigning the major peaks to specific types of bonds, determining the functional
group(s) present in the molecule, and drawing or recognizing a reasonable
structure for the molecule. (NOTE: This material was presented during Unit
1. You will be responsible for using
this material to complete the two IR assignments at the end of Unit 1 and the
beginning of Unit 2. You will be
responsible for this objective on the Unit 2 exam.) NOTE: Beginning in Unit 3, you will be responsible
for knowing the major IR stretching frequencies for organic molecules.
20.
You will be
able to answer questions or solve problems incorporating material from previous
units in Organic Chemistry and/or General chemistry with the current unit
objectives.
UNIT 3: Stereochemistry
Homework Problems: 5-2,
5-3, 5-5, 5-6, 5-8, 5-9, 5-13, 5-14, 5-16, 5-17, 5-18, 5-19, 5-20,
5-21, 5-22 (omit d), 5-23, 5-26, 5-27, 5-30, 5-31 (omit d, e), 5-32, 5-33, 5-34,
5-35a
NOTE:
Homework problems shown in bold type are ones that you MUST do. The others listed are highly recommended for
those students who want to do well on the unit quiz and exam.
1.
Define and/or
recognize definitions of the terms given in the glossary at the end of the
reading assignment. Recognize or give
examples of each.
2.
Identify all
chiral carbon atoms present in a molecule.
Assign (R) and (S) designations to each chiral carbon. Designate the internal mirror plane of
symmetry present in a molecule.
Identify a given molecule as chiral, achiral, optically active, or not
optically active.
3.
Draw three
dimensional structures for molecules which have chiral carbon centers.
4.
Correctly name
compounds with one or more chiral carbons using (R) - (S) designations.
5.
Identify the
relationship between two structures and classify them as representing
structural (constitutional) isomers, enantiomers, diastereomers, molecules of
the same compound, or different compounds that are not isomers.
6.
Given the
formula of a cyclic or acyclic compound with one or more stereocenter, draw
three dimensional structures for all of the possible isomers or stereoisomers. Identify the relationships between the
structures drawn (structural isomers, enantiomers, diastereomers).
7.
Calculate the
percent optical purity of a chiral substance when given the optical rotation of
the pure compound and the optical rotation of a sample of that compound. Calculate the enantiomeric excess when given
the relative amounts of a pair of enantiomers.
Calculate the relative proportions of a mixture of enantiomers required
to produce a specified optical rotation.
8.
Compare and
contrast enantiomers and diastereomers in terms of the following properties:
(a) melting and boiling points
(b) density
(c) refractive index
(d) behavior toward plane-polarized light
9.
Describe how
the resolution of enantiomers may be accomplished.
10.
You will know the major IR stretching frequencies for
organic molecules. You will be able interpret the IR spectrum
for an organic compound by assigning the major peaks to specific types of
bonds, determining the functional group(s) present in the molecule, and drawing
or recognizing a reasonable structure for the molecule.
11.
You will be
able to answer questions or solve problems incorporating material from previous
units in Organic Chemistry and/or General chemistry with the current unit
objectives.
UNIT 4: Nucleophilic
Substitution and Elimination Reactions
Homework Problems: 6-1, 6-7, 6-9a, 6-10, 6-11, 6-14, 6-15, 6-16, 6-19, 6-20, 6-21, 6-24, 6-26, 6-27, 6-30a, 6-33, 6-37, 6-40, 6-42, 6-43, 6-44, 6-45,
6-46, 6-48, 6-49, 6-51, 6-52, 6-53,
6-54, 6-55, 6-56, 6-60, 6-61, 6-66, 6-74
NOTE:
Homework problems shown in bold type are ones that you MUST do. The others listed are highly recommended for
those students who want to do well on the unit quiz and exam.
1.
Define and/or
recognize definitions of the terms given in the glossary at the end of the
reading assignment. Recognize or give
examples of each.
2.
Given the
structure of an alkyl halide, write the correct IUPAC name for the
compound. Given the name of an alkyl
halide, draw the correct structure of the compound. Given the name or structure of an alkyl
halide, designate it as primary, secondary, tertiary, allylic, benzylic, vinyl,
aryl, geminal, and/or vicinal. Correctly
specify or draw the stereochemistry of an alkyl halide, as appropriate.
3.
Predict and
apply general trends in physical properties of alkyl halides.
4.
Given the name
or formula of a molecule or ion, draw the Lewis structures for the substance
and determine if it is a potential nucleophile.
5.
Rank specified
carbocations (carbonium ions) based on their relative stabilities.
6.
Predict the
major product formed by free radical halogenation and free radical allylic
halogenation. Identify the most
appropriate hydrocarbon and reagents needed to prepare a specified alkyl
halide.
7.
Draw the
mechanisms for SN1, SN2, E1, and E2 reactions and account
for the stereochemistry of the reactions and any rearrangements that occur.
8.
Given
reactants and reaction conditions for nucleophilic substitution or elimination
reactions, predict the structure of the product(s). If more than one product can be formed,
predict the major and minor products.
Identify the mechanism by which the reaction would proceed (SN1,
SN2, E1, or E2).
9.
Use IR
spectroscopy to predict the structure of the product formed during a reaction
or sequence of reactions. Identify the
reagents needed to convert a given substrate into a product consistent with the
given IR. You will not have access to the table of major IR stretching frequencies.
10. Outline the synthesis of specified compounds by nucleophilic
substitution and elimination reactions, including selecting the appropriate
reactants, specifying appropriate reaction conditions, and identifying major
and minor products. Where necessary, specify reaction conditions that would
result in the specified compounds being formed as the sole or major product.
11. Recognize and describe the effects of substrate, solvent,
nucleophile, concentration of reactants, temperature, and leaving group on the
various types of substitution and elimination reactions.
12. State or recognize the factors that determine the strength
of nucleophiles and rank nucleophiles by strength.
13. Use reaction-energy diagrams of substitution and elimination
reactions to identify the overall reaction order, the presence or absence of a
reactive intermediate, the activation energy, the rate determining step, and
the heat of reaction.
14. Describe the relationship between the rate equation and the
transition state.
15. Given the equation for a nucleophilic substitution or
elimination reaction, identify the reaction as 1st or 2nd
order and predict the impact that changes in the concentration of reactants
will have on the rate of the reaction.
16. Predict which member of a group of alkyl halides would react
most rapidly by the SN2 mechanism and explain why. Predict which member of a group of alkyl
halides would react most rapidly by the SN1 mechanism and explain
why.
17. Given groups of SN1 reactions or groups of SN2
reactions, predict which reaction would occur more rapidly and explain why.
18. You will be able to answer questions or solve problems
incorporating material from previous units in Organic Chemistry and/or General
chemistry with the current unit objectives.
UNIT 5: Alkenes and Alkynes: Structure,
Synthesis, and Reactions
Homework Problems:
7-3, 7-4, 7-5 (e-j), 7-6, 7-10, 7-11, 7-12, 7-13, 7-15, 7-17, 7-19, 7-22, 7-23, 7-24b,
7-25 (a-c), 7-29, 7-31, 7-32, 7-33, 7-38, 7-39, 7-40, 7-41, 7-42,
7-43a, 7-44, 7-45, 7-46, 7-53, 8-1, 8-4, 8-6, 8-7, 8-8, 8-9, 8-10, 8-11, 8-18,
8-21, 8-22, 8-23, 8-29, 8-32, 8-34, 8-47(omit o), 8-48 (b, c, g), 8-49, 8-50, 8-59, 8-61, 8-66, 9-5, 9-7, 9-8, 9-12, 9-16, 9-18, 9-21,
9-27, 9-29, 9-33 (omit a,e ), 9-34,
9-36, 9-37
NOTE:
Homework problems shown in bold type are ones that you MUST do. The others listed are highly recommended for
those students who want to do well on the unit quiz and exam.
1.
Define and/or
recognize definitions of the terms given in the glossary at the end of the
reading assignment. Recognize or give
examples of each.
2.
Apply IUPAC
conventions to naming and drawing structures of specified alkenes, cycloalkenes,
and alkynes. Use in proper context the names ethylene, propylene, isobutylene,
acetylene, and vinyl, methylene and allyl groups. Include the specifications
cis, trans, (E), and (Z) in names and structures where appropriate in alkenes
and cycloalkenes. Correctly specify or
draw the stereochemistry of any asymmetric carbons present.
3.
State or
recognize the types of bonds, hybrid orbitals, and geometry of alkenes and
alkynes.
4.
Predict the
physical properties of alkenes and alkynes.
5.
Calculate the
elements of unsaturation for specified compounds. Given a molecular formula, calculate
its elements of unsaturation and predict its structure (or possible
structures).
6.
For specified
pairs of alkenes and cycloalkenes, including cis and trans isomers, identify
the compound that should be more stable based on such data as heats of
hydrogenation, heats of combustion, degree of substitution, geometry, and ring
size. State or recognize statements describing the general trends in the
stability of alkenes and cycloalkenes.
7.
Predict the
major product in the following reactions by which alkenes can be prepared:
·
dehydrohalogenation
of alkyl halides
·
dehydration of
alcohols
·
dehalogenation
of vicinal dibromides.
8.
Given
reactants and reaction conditions, predict the product(s) of the following
addition reactions of alkenes. Apply Markovnikov's Rule where it is applicable
to predicting major products of reactions. If syn or anti additions take place
apply those principles to predicting the outcome of the reaction.
a.
Catalytic
hydrogenation
b.
Addition of HX
c.
Anti-Markovnikov
addition of HBr
d.
Addition of
bromine and chlorine
e.
Acid-catalyze
hydration
f.
Oxymercuration-demercuration
g.
Alkoxymercuration-demercuration
h.
Hydroboration
oxidation
i.
Formation of
halohydrins
j.
Epoxidation
k.
Anti
hydroxylation (Preparation of anti vicinal diols via epoxidation and
hydrolysis)
l.
Preparation of
syn vicinal diols (syn hydroxylation)
m.
Formation of
cyclopropanes
n.
Oxidative
cleavage
o.
Ozonolysis
9.
Write logical
mechanisms for the following reactions and account for the stereochemistry of
the reactions and any rearrangements that occur:
·
dehydrohalogenation
·
dehalogenation
·
acid catalyzed
dehydration of an alcohol
·
halogenation
·
addition of HX
to an alkene
·
oxymercuration-demercuration
·
acid catalyzed
hydration (hydrolysis) of an alkene
10.
Identify the
best reagents and conditions needed to produce an alkene or convert an alkene
to another functional group using one or more of the reactions identified in
objectives 7 and 8.
11.
Describe the
function of the catalyst in hydrogenation reactions and distinguish between syn
and anti additions.
12.
Describe with
equations simple chemical tests (solubility in cold concentrated sulfuric acid,
reaction with bromine in carbon tetrachloride, oxidation by cold dilute
potassium permanganate, and reaction with ethanolic silver nitrate) that would
distinguish between specified alkanes, alkenes, and alkyl halides.
13.
Identify the
relative acidities of alkanes, alkenes, and alkynes and explain their relative
pKa's. Be able to show how to generate
and utilize acetylide (alkynide) ions.
14.
Predict the
major product in the following reactions by which alkynes can be synthesized:
a.
alkylation of
acetylide (alkynide) ions including formation of the acetylide ion
b.
addition of
acetylide ions to carbonyls and epoxides
c.
double
dehydrohalogenation of alkyl halides.
15.
Given
reactants and reaction conditions, predict the product(s) of the following
reactions of alkynes:
a.
hydrogenation
to alkanes or cis-alkenes
b.
alkali metal
reduction of alkenes to trans-alkenes
c.
addition of
halogens
d.
addition of
hydrogen halides
e.
anti-Markovnikov
addition of HBr
f.
acid hydration
g.
hydroboration-oxidation
16.
Draw the
mechanism for the following reactions:
a. formation of an
acetylide ion
b. reaction of an
acetyide ion with an alkyl halide, epoxide, aldehyde, or ketone
c. addition of
hydrohalic acid to an alkyne
d. acid or base
catalyzed keto-enol tautomerism
17.
Identify the
best reagents and conditions needed to produce a specified alkyne or convert an
alkyne to another functional group using the reactions identified in objectives
13-15.
18.
Apply one or
more of the reactions listed in objectives 7, 8, 13, 14, and 15 as well as
those covered in previous units to the single- or multi-step synthesis of
specified compounds.
19.
Use IR
spectroscopy to predict the structure of the product formed during a reaction
or sequence of reactions. Identify the
reagents needed to convert a given substrate into a product consistent with the
given IR. You will not have access to
the table of major IR stretching frequencies.
20. You will be able to answer questions or solve problems
incorporating material from previous units in Organic Chemistry and/or General
chemistry with the current unit objectives.
UNIT 6: The Chemistry of Alcohols and
Ethers
Homework Problems:
10-9, 10-10, 10-12, 10-13, 10-14, 10-15, 10-17, 10-19, 10-22, 10-23, 10-24, 10-25, 10-28, 10-31, 10-32, 10-33, 10-34,
10-36, 10-37, 10-38, 10-39, 10-40,
10-42, 10-49, 10-51, 10-52, 11-1, 11-2,
11-5, 11-6, 11-9, 11-10, 11-12, 11-14, 11-15, 11-21, 11-22, 11-28a, 11-31, 11-33, 11-38, 11-40, 11-41, 11-42,
11-43, 11-44, 11-48, 11-49, 11-51, 11-52, 11-53, 14-4, 14-9, 14-10,
14-19, 14-26, 14-27, 14-28, 14-30,
14-31, 14-32, 14-33 (omit a – e), 14-34, 14-37, 14-38, 14-39,
14-41, 14-42
NOTE:
Homework problems shown in bold type are ones that you MUST do. The others listed are highly recommended for those
students who want to do well on the unit quiz and exam.
1.
Define and/or
recognize definitions of the terms given in the glossary at the end of the
reading assignment. Recognize or give
examples of each.
2.
Given a
formula for an alcohol, diol, phenol, or thiol, write the correct IUPAC
name. Given the name of one of these
compounds, draw the structure. Use in
proper context the names (and corresponding structures): ester, sulfonate,
tosylate, alkyl phosphates, sulfates, nitrate ester, pinacol, catechol,
resorcinol, cresols, and hydroquinone.
3.
Draw and name
ethers and heterocyclic ethers, including epoxides and crown ethers.
4.
Be able to
predict relative boiling points and other physical properties of alcohols and ethers.
5.
Given
reactants and reaction conditions, predict the products of the following types
of reactions used to form alcohols. In
each case, be able to give the stereochemistry of the product.
a.
nucleophilic substitution of alkyl halides
b.
acid-catalyzed hydration of alkenes
c.
oxymercuration-demercuration of alkenes
d.
hydroboration-oxidation of alkenes
e.
hydrolysis of epoxides to form anti vicinal diols (anti hydroxylation
of alkenes)
f.
syn hydroxylation of alkenes
g.
synthesis of Grignard reagents & alkyl lithium reagents and
addition of these organometallic reagents to formaldehyde, aldehydes, ketones,
esters, acid chlorides, and epoxides
h.
reduction of carbonyl compounds
6.
Recognize,
describe, or predict the products formed during the side reactions of
organometallics and the limitations they place on the reactions of
organometallic reagents.
7.
Given
reactants and reaction conditions for each of the following kinds of reactions
of alcohols or derivatives of alcohols, predict the product of the reaction.
a.
Oxidation of
primary alcohols to aldehydes or carboxylic acids
b.
Oxidation of
secondary alcohols to ketones
c.
Formation of
alkyl halides from the reactions of alcohols with hydrohalic acids, phosphorus
halides, and thionyl chloride
d.
Formation of
alkyl sulfonates (for example, tosylates)
e.
Reactions of
alkyl sulfonates in substitution and elimination reactions
f.
Acid catalyzed
dehydration of alcohols
g.
Esterification
of alcohols
h.
Formation of
alkoxide ions
i.
Williamson
ether synthesis
j.
Pinacol
rearrangement
k.
Periodic acid
cleavage of glycols
8.
Identify
oxidizing and reducing agents. Determine
if a reaction is an oxidation or reduction and specify the most appropriate
reagent for a particular conversion.
9.
Given
reactants and reaction conditions, predict the products of the following types
of reactions used to form ethers and epoxides:
a.
Williamson
ether synthesis
b.
alkoxymercuration-demercuration
c.
epoxidation
d.
base-promoted
cyclization of halohydrin
e.
Intermolecular
dehydration of alcohols
10.
Given
reactants and reaction conditions for each of the following kinds of reactions
of ethers and epoxides, predict the product of the reaction.
a.
cleavage of
ethers with hydrohalic acids
b.
acid-catalyzed
ring opening of epoxides
c.
base-catalyzed
ring openings of epoxides
d.
addition of
organometallic reagents to epoxides
11.
Write the
mechanism for the following reactions:
a.
Reactions of
alkyl sulfonates (for example, tosylates) in SN2 or E2 reactions
b.
Acid catalyzed
dehydration of alcohols
c.
Formation of
alkyl halides by the reaction of an alcohol with HX, PBr3, or
thionyl chloride
d.
Pinacol
rearrangement
e.
Williamson
ether synthesis including the formation of the alkoxide ion
f.
Acid-catalyzed
ring opening of epoxides in alcohol
g.
Base-catalyzed
ring opening of epoxides in alcohol
12.
Identify the
best reagents and conditions needed to produce an alcohol, ether, or epoxide or
to convert an alcohol, ether, or epoxide into another functional group using
one or more of the reactions studied during this unit.
13.
Describe the
autooxidation reactions of ethers.
Explain the dangers of handling ethers and methods to minimize these
hazards.
14.
Apply one or
more of the reactions listed in objectives 5, 7, 9, and 10 as well as those
covered in previous units to the single- or mulit-step synthesis of specified
compounds.
15.
Use IR
spectroscopy to predict the structure of the product formed during a reaction
or sequence of reactions. Identify the
reagents needed to convert a given substrate into a product consistent with the
given IR. You will not have access to
the table of major IR stretching frequencies.
16.
You will be
able to answer questions or solve problems incorporating material from previous
units in Organic Chemistry and/or General chemistry with the current unit
objectives.
Objectives
for Comprehensive Final Exam
Objectives from
Organic I:
1.
Draw or
recognize the formula (structural, condensed, or line-angle) of organic
compounds belonging to the families listed below. Be able to classify compounds according to
their functional group and to identify all of the functional groups present in
a compound:
alkanes
ketones aldehydes
cycloalkanes carboxylic
acids acid chlorides
alkenes esters ethers
alkynes amines alcohols
alkyl halides amides nitriles
2.
Interpret the
IR spectrum for an organic compound by assigning the major peaks to specific
types of bonds, determining the functional group(s) present in the molecule,
and drawing or recognizing a reasonable structure for the molecule. You will not
have access to the table of major IR stretching frequencies.
3.
Draw the Lewis
structure for a specified molecule or ion and position formal charges on atoms.
Be able to draw resonance structures for representative compounds, ions, or
free radicals.
4.
Predict the
shape of a molecule using VSEPR theory.
From the shape of the molecule and the electronegativities of the bonded
atoms, predict if the molecule is polar or nonpolar and identify the direction
of any molecular dipole moment.
5.
Relate
intermolecular forces to boiling points and solubilities of organic
compounds. Rank a series of compounds in
order of boiling point or solubility in a specified solvent.
6.
Predict the
type of bond hybridization, if any, occurring in compounds in which C, N, and O
are the central atoms and be able to predict the geometry of the bond.
7.
Given a
compound represented as a structural formula, condensed formula, line-angle
drawing, or three-dimensional structure, represent the molecule using any of
the other possible structures or formulas.
8.
Given a
chemical reaction, identify the Lewis and Bronsted-Lowry acids and bases that
are present. Be able to recognize common
acids used in organic synthesis including carboxylic acids, phenols, alcohols,
inorganic acids, and water. Be able to
recognize common bases used in organic synthesis including amines, alcohols,
water and those containing hydroxide, alkoxide, hydride, and amide ions.
9.
Given the
reactants in an acid/base reaction be able to give the structures and/or
formulas of the products of the reaction. Be able to use curved arrows to show the
formation of the products.
10.
Apply IUPAC
conventions for the nomenclature of alkanes, cycloalkanes, alkyl halides,
alkenes, alkynes, alcohols and ethers.
Include (R) - (S) designations for chiral carbons of specified compounds,
as appropriate. Include the
specifications cis, trans, (E), and (Z) in names and structures where
appropriate in alkenes and cycloalkenes.
11.
Draw and/or
recognize the Newman projections representing the staggered, skew, and eclipsed
conformations of ethane, and the anti-, gauche, and eclipsed conformations of
butane.
12.
Draw and/or
recognize drawings of the chair, boat, and twist-boat conformations of
cyclohexane. Identify axial and equatorial hydrogens on the chair conformation.
Predict which of the two possible chair forms of a monosubstituted cyclohexane
is more stable.
13.
Draw and/or
recognize drawings of the cis and trans isomers of disubstituted cycloalkanes
and of the alternate chair conformations of each isomer. Predict which of the
alternate chair conformations is the more stable.
14.
Draw the
complete mechanism for free radical halogenation of any alkane or cylcoalkane.
15.
Use the
relative stability of methyl, primary, secondary, tertiary, allyl, substituted
allylic, and vinyl free radicals and carbocations (carbonium ions) to rank a
series of free radicals or carbocations in order of stability.
16.
Predict the
major product formed by free radical halogenation of an alkane or cycloalkane.
17.
Be able to
draw and/or use an energy profile to discuss or determine the transition
states, activation energy, intermediates, heat of reaction, and the rate
determining step of a reaction.
18.
Identify all
chiral carbon atoms present in a molecule.
Assign (R) and (S) designations to each chiral carbon. Designate the internal mirror plane of
symmetry present in a molecule.
Identify a given molecule as chiral, achiral, optically active, or not
optically active. Draw three dimensional
structures for molecules which have chiral carbon centers.
19.
Identify the
relationship between two structures and classify them as representing
structural (constitutional) isomers, enantiomers, diastereomers, molecules of
the same compound, or different compounds that are not isomers.
20.
Given the
formula of a cyclic or acyclic compound with one or more stereocenter, draw
three dimensional structures for all of the possible isomers or
stereoisomers. Identify the
relationships between the structures drawn (structural isomers, enantiomers,
diastereomers).
21. Write Lewis structures for specified molecules and ions and
indicate which are potential nucleophiles.
Given the formula of a molecule or ion, identify if it is a potential
nucleophile.
22. Given the equation for a nucleophilic substitution or
elimination reaction, identify the reaction as 1st or 2nd
order and predict the impact that changes in the concentration of reactants
will have on the rate of the reaction.
23. Predict which member of a group of alkyl halides would react
most rapidly by the SN2 mechanism and explain why. Predict which member of a group of alkyl
halides would react most rapidly by the SN1 mechanism and explain
why.
24. Given groups of SN1 reactions or groups of SN2
reactions, predict which reaction would occur more rapidly and explain why.
25. Outline the synthesis of a specified alkyl halide or predict
the structure of the alkyl halide formed by a specified reaction.
26. Draw the mechanisms for SN1, SN2, E1,
and E2 reactions and account for the stereochemistry of the reactions and any
rearrangements that occur.
27. Given reactants and reaction conditions for nucleophilic
substitution or elimination reactions, predict what product(s) would be
formed. If more than one product can be
formed, predict the major and minor products.
Identify the mechanism by which the reaction would proceed (SN1,
SN2, E1, or E2).
28. Outline the synthesis of specified compounds by nucleophilic
substitution and elimination reactions, including selecting the appropriate
reactants, specifying appropriate reaction conditions, and identifying major
and minor products.
29.
Predict the
major product in the following reactions by which alkenes can be prepared:
a.
dehydrohalogenation
of alkyl halides
b.
dehydration of
alcohols
c.
dehalogenation
of vic-dibromides.
30.
Be able to
write logical mechanisms for the following reactions that use or form alkenes
and be able to account for the stereochemistry of the reactions and any
rearrangements that occur:
a.
Dehydrohalogenation
b.
Dehalogenation
c.
Acid catalyzed
dehydration of an alcohol
d.
Acid catalyzed
hydration (hydrolysis) of an alkene
e.
Hydrohalogenation
of an alkene
f.
Halogenation
of an alkene
g.
Oxymercuration-demercuration
31.
Given the
structure of an alkene and reaction conditions, predict the product(s) of or
know the reactions for the following kinds of addition reactions. Apply Markovnikov's Rule where it is
applicable to predicting major products of reactions. If syn or anti additions
take place apply those principles to predicting the outcome of the reaction.
a.
Catalytic
hydrogenation
b.
Addition of HX
c.
Anti-Markovnikov
addition of HBr
d.
Addition of bromine
or chlorine
e.
Acid-catalyzed
hydration
f.
Oxymercuration-demercuration
g.
Alkoxymercuration-demercuration
h.
Hydroboration
oxidation
i.
Formation of
halohydrins
j.
Epoxidation
k.
Anti
hydroxylation
l.
Preparation of
syn vicinal diols (syn hydroxylation)
32.
Predict the major
product in the following reactions by which alkynes can be synthesized:
a.
Formation and
alkylation of acetylide (alkynide) ions
b.
addition of
acetylide ions to carbonyls and epoxides
c.
double
dehydrohalogenation of alkyl halides.
34.
Given
reactants and reaction conditions, predict the product(s) of the following
reactions of alkynes:
a.
catalytic hydrogenation
of alkynes to alkanes or cis-alkenes
b.
alkali metal
reduction of alkynes to trans-alkenes
c.
addition of
halogens
d.
addition of
hydrogen halides
e.
anti-Markovnikov
addition of HBr
f.
acid hydration
g.
hydroboration-oxidation
h.
oxidation of
alkynes
35. Draw a reasonable mechanism for the following reactions of
alkynes:
a. formation and
alkylation of acetylide (alkynide) ions
b. addition of
acetylide ions to carbonyls, epoxides, or alkyl halides
36. Given reactants and reaction conditions, predict the
products of the following types of reactions and/or use these reactions to
outline the synthesis of specified alcohols. In each case, be able to give the
stereochemistry of the product.
a.
nucleophilic substitution on alkyl halides
b.
acid-catalyzed hydration of alkenes
c.
oxymercuration-demercuration of alkenes
d.
hydroboration-oxidation of alkenes
e.
acid catalyzed hydration of alkenes
f.
Grignard reagents & alkyl lithium with formaldehyde, aldehydes,
ketones, esters, acid chlorides, and epoxides
g.
reduction of carbonyl compounds
37.
Given
reactants and reaction conditions for each of the following kinds of reactions
of alcohols or derivatives of alcohols, predict the product of the reaction.
a.
Oxidation of
primary alcohols to aldehydes or carboxylic acids
b.
Oxidation of
secondary alcohols to ketones
c.
Formation of
alkyl halides from the reactions of alcohols with hydrohalic acids, phosphorus
halides, and thionyl chloride
d.
Formation of
alkyl sulfonates (for example, tosylates)
e.
Reactions of
alkyl sulfonates in SN2 reactions or E2 reactions
f.
Acid catalyzed
dehydration of alcohols
g.
Esterification
of alcohols
h.
Formation of
alkoxide ions
38.
Given
reactants and reaction conditions, predict the products of the following types
of reactions used to form ethers and epoxides:
a.
Williamson
ether synthesis
b.
alkoxymercuration-demercuration
c.
epoxidation
d.
base-promoted
cyclization of halohydrin
39.
Given
reactants and reaction conditions for each of the following kinds of reactions
of ethers and epoxides, predict the product of the reaction.
a.
acid-catalyzed
ring opening of epoxides
b.
base-catalyzed
ring openings of epoxides
c.
addition of
organometallic reagents to epoxides
40.
Write the
mechanism for the following reactions:
a.
Reactions of
alkyl sulfonates (for example, tosylates) in SN2 or E2 reactions
b.
Acid catalyzed
dehydration of alcohols
c.
Formation of
alkyl halides by the reaction of an alcohol with HX, PBr3, or
thionyl chloride
d.
Williamson
ether synthesis including formation of the alkoxide ion
e.
Acid-catalyzed
ring opening of epoxides in alcohol
f.
Base-catalyzed
ring opening of epoxides in alcohol
41.
Given the name
and/or structure of a desired product, be able to apply one or more of the
reactions covered in these objectives to synthesize the product from a
designated starting material.
42.
Use IR
spectroscopy to predict the structure of the product formed during a reaction
or sequence of reactions. Identify the
reagents needed to convert a given substrate into a product consistent with the
given IR. You will not have access to the table of major IR stretching frequencies.
General Chemistry
Objectives for Comprehensive Final:
1. Given the appropriate conversion
factors, you will be able to use dimensional analysis to convert from one set
of units to another. You will know the
numerical value for and be able to apply the common metric-metric conversions
for micro, milli, centi, kilo, and mega. (Chem 1)
2. Given two of the three variables –
density, mass, and volume – you will be able to calculate the third. (Chem 1)
3. Given the name of an ionic compound,
inorganic acid, or binary molecular compound, you will be able to write its
formula. Given the formula for an ionic
compound, inorganic acid, or binary molecular compound, you will be able to
write its name. (Chem 1/Chem 2)
4. You will be able to calculate the
molarity of a solution when given the mass of solute and the total volume of
solution. (Chem 1/Chem 2)
5. You will be able to calculate the
volume of a stock solution needed to prepare a specified volume of a more
dilute solution. You will be able to
calculate the concentration of a solution prepared by the dilution of a more
concentrated solution. (Chem 1/Chem 2)
6. You will be able to work the
following types of stoichiometry problems:
mass-mass, mass-mole, mole-mole, mass-volume, volume-mole, and
volume-volume. (Chem 1/Chem 2)
7. Given DHof, So,
or DGof,
you will be able to calculate the standard enthalpy change, entropy change, or
Gibbs free energy change that occurs for a specified reaction. (Chem 2)
8. Given the appropriate calorimetry
data, you will be able to calculate the specific heat, heat of solution, or
heat of combustion for a given substance. (Chem 2)
9. Given a thermochemical equation, you
will be able to calculate the enthalpy change that occurs for a reaction
involving a specified amount of a reactant or product for either the forward or
reverse reactions. (Chem 2)
10. Given the name or structure of a
compound, you will be able to identify the intermolecular forces that exist
between molecules of the compound and will be able to determine which
intermolecular force has the greatest impact on its physical properties. (Chem
2)
11. Given appropriate data, you will be
able to calculate the value of an equilibrium constant. You will be able to use the value of K to
determine if the reaction favors the formation of reactants or products. (Chem 2)
12. Given a reaction at equilibrium and
whether it is exothermic or endothermic, you will be able to apply
LeChatelier’s principle to predict the direct in which the reaction will shift
due to disturbances such as a temperature change, a change in the amount of a
reactant or product, a change in the volume of the system, or the addition of a
catalyst. (Chem 2)
13. Given the concentration of a
reactant or product of a chemical reaction as a function of time, you will be
able to calculate the average reaction rate for a specified time interval. (Chem 2)
14. Given a rate law expression for a
chemical reaction or general information about the kinetics of the reaction, you
will be able to determine how a new set of reactant concentrations will affect
the reaction rate. (Chem 2)
15. You will be able to determine
relative acid strengths using the values of Ka or pKa.
16. Given the concentration of an
aqueous solution of a strong acid or strong base, you will be able to calculate
[H+], [
17. Given a redox reaction, you will be
able to identify the element oxidized or reduced as well as the oxidizing agent
(oxidant) or reducing agent (reductant).
(Chem 1/Chem 2)
NOTE:
Homework problems shown in bold type are ones that you MUST do. The others listed are highly recommended for
those students who want to do well on the unit quiz and exam.
Unit 1
Chapter 12 (Sections
12-1 to 12-12)
Homework: 1-6, 1-7 (d,e,g), 1-9, 1-10, 1-11, 1-12, 1-15, 1-18, 1-19, 1-21, 1-23, 1-25, 1-26, 1-27, 1-28, 1-34, 1-35, 1-36, 1-37, 1-40, 1-41, 1-42. 1-43, 1-44, 1-45, 1-46, 1-47, 2-5, 2-14, 2-16, 2-17,
2-18, 2-20, 2-21, 2-22, 2-27, 2-28, 2-36, 2-37, 2-39, 2-40, 2-41,
2-42, 2-44,
IR Homework: 12-2,
12-3, 12-4, 12-5, 12-6, 12-15 (omit a & b), 12-16
Unit 2
Chapter 12 (Sections 12-1
to 12-12)
Homework Problems: 3-2, 3-3, 3-4, 3-5, 3-6, 3-9, 3-14,
3-15, 3-17, 3-21, 3-24, 3-27, 3-28, 3-29, 3-30, 3-33, 3-34, 3-37, 3-38, 3-44; 4-2a, 4-4a, 4-9a, 4-11, 4-12, 4-13, 4-14, 4-15, 4-25,
4-29, 4-35, 4-37, 4-39, 4-41, 4-42,
4-43, 4-44, 4-45, 4-46.
IR Homework: 12-2,
12-3, 12-4, 12-5, 12-6, 12-15 (omit a & b), 12-16
UNIT 3: Stereochemistry
Homework Problems: 5-3, 5-5, 5-6,
5-8, 5-9, 5-12, 5-13, 5-14 (d,e,f),
5-16, 5-17, 5-18, 5-19, 5-20, 5-21, 5-22, 5-23, 5-26, 5-27,
5-30,5-31 (omit d,e), 5-32, 5-33, 5-34, 5-35 (a,b)
UNIT 4:
Nucleophilic Substitution and Elimination Reactions
Homework Problems: 6-1, 6-2, 6-3, 6-6, 6-7, 6-9a, 6-10, 6-11, 6-12, 6-14, 6-15, 6-16, 6-19, 6-20,
6-23, 6-24, 6-26, 6-27, 6-29, 6-33, 6-37, 6-38, 6-40, 6-42, 6-43, 6-44, 6-45, 6-46, 6-47, 6-48, 6-49, 6-51, 6-52, 6-53, 6-56, 6-60, 6-61, 6-66, 6-73, 6-75
(b,c)
UNIT 5: Alkenes and Alkynes: Structure,
Synthesis, and Reactions
Homework Problems:
7-1, 7-4, 7-8, 7-10, 7-11 a-e, 7-12, 7-13, 7-15, 7-17, 7-19, 7-22, 7-24, 7-25, 7-28, 7-29, 7-31, 7-32, 7-33, 7-34a,
7-36, 7-37, 7-38, 7-39, 7-40, 7-41, 7-45, 7-46, 7-53; 8-1, 8-4,
8-8, 8-9, 8-11, 8-13, 8-18, 8-21, 8-23, 8-29, 8-32, 8-34, 8-37, 8-47, 8-48 (b, c, e, g), 8-49,
8-50, 8-59, 8-61; 9-5, 9-7, 9-8,
9-13, 9-21, 9-27, 9-29, 9-30, 9-33, 9-34, 9-36, 9-37, 9-40.
UNIT 6: The Chemistry of Alcohols and
Ethers
Homework Problems:
10-3, 10-10, 10-12, 10-13, 10-14, 10-15, 10-17, 10-19, 10-22, 10-23, 10-24, 10-25, 10-28, 10-31, 10-32, 10-33, 10-34, 10-35, 10-36,
10-37, 10-38, 10-39, 10-40, 10-42,
10-49, 10-51; 11-1, 11-2,
11-6, 11-9, 11-10, 11-12, 11-13, 11-15, 11-21, 11-22, 11-28, 11-30, 11-31, 11-38,
11-41, 11-42, 11-43, 11-44, 11-47, 11-48,
11-49, 11-51, 11-52, 11-53; 14-4,
14-6, 14-9, 14-10, 14-15, 14-19,
14-25, 14-26, 14-27, 14-28, 14-30, 14-34,
14-38, 14-39, 14-41.
Grade Record:
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to keep track of your grades.
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